Looked for a place to sit after pride parade- no easy feat. This place was a cute local dive, and bartender (Jason I think?) was awesome. I was melting and asked for "something with effen cucumber"- and I got an insanely strong, insanely delicious concoction. Downside- place is too quiet if you don't play jukebox. And the manager wouldn't let bartender put on the radio. Only one bathroom stall, but that's to be expected for small spot. Also, not sure if it was bc pride, but getting drinks in red solo cups indoors is just insulting. I wasn't sitting at the kids table, and if I'm paying Chicago bar prices, can I at least get a plastic cup a step above beer pong? read more

This is my neighborhood dive! Friendly faces, affordable drinks, and an atmosphere that reminds me of my family's old bar. They have an "all-occasions" tree that they keep up year-round. How awesome is that. I haven't met "Jackie" yet, but I've heard she's a doll. This place is a hidden treasure. read more

This is a nice hidden gem in Lakeside. Orlando is the man! Prices are good, drink selections are good, and environment is everything you want in a local bar. read more

I had the pleasure of stopping in for a drink on a Saturday night. It is a small (and by small I mean tiny) little corner bar. We were hesitant at first, because it was so small we were wondering how welcoming it would be to outsiders. But much to our pleasant surprise they welcomed us with open arms and dance moves! The bartender was personable and as attentive as he could be given he was the only one behind the bar. Patrons were polite, social, cordial and inviting. If I lived in the neighborhood I could absolutely see this becoming my regular watering hole. If you're looking for a hopping club on Broadway... keep going, but if you just want a couple drinks with laughter and fun in a relaxed, casual, borderline runned down atmosphere c'mon in and pull up a stool, you will have a blast! read more

This is the best neighborhood bar around! My coworkers and I come here all the time to see our favorite bartenders: Greg and Jason! They're friendly (yet sarcastic when called for) and make great drinks. I call Greg Google because he knows a bit about EVERYTHING (seriously, anything) and Jason has a special place in my heart because he always makes food to share with the bar and sometimes will cater to my crazy vegan diet! I love going to a bar where you're guaranteed to see some familiar faces and can just unwind with your friends. P.S. Jason makes the best-- bar none, the absolute BEST Bloody Mary you'll ever have in your life. I've had many a Bloody-- and not one comes close to Jason's! Seriously. Order one. read more

The bartender with the horrible mustache was an asshole. Won't make a margarita. I'll definitely be back.

We went in here because my date had to pee...left after some Jeppson's Malort. yeah read more

Jacqueline's - puts hair on your chest - Dive Bars Near Me - Chicago, Illinois

Only reason this is a 4 vs. 5 is my personal favorite bars include top notch music (live or juke box), no TVs, and comfy seating (vs barstools...I'm short, barstools are painful). J is the BEST bartender - he greeted us on our 1st visit as if we were regulars, and treated us like gold. And he makes great drinks btw ;-) I've walked past this place daily for the 9 months I've lived here, but never entered. Several times regulars at the bar have stopped me and my dog to chat and mention the bar lets dogs inside. So...last week, after working 60hrs in 3 days, I agreed to grab a drink with a friend on the condition we go to Jacqueline's since my dog had been cooped up inside so much that weekend. My dog was allowed to roam freely, was handed dog bisquits throughout the evening, and low and behold, 1 drink turned into several until 2am. So much fun - J also is a great cook who likes to bring in his latest masterpiece for the customers to enjoy. I highly recommend this place to anyone looking for a low-key, friendly place to grab a drink, chat with a friend, run into a neighbor, and share with their dog. read more

COCKROACHES. Multiple cockroaches literally crawled across the floor and on the bar and the bartender didn't seem to care at all. The building has to have cockroach problems because I've also seen them in the neighboring Mexican restaurant. The bartender is nice but odd. Was extremely grossed out by the bugs and won't be returning. read more

Cute little neighborhood dive bar. Judgment-free zone. It's true that it's diverse. The only thing is there were three people makong out with each other (that's putting it lightly) and the bar tender seemed to avoid looking in their direction. They were NASTY. But I guess we let em be since they have a sign that says No Drama lol. I would go back though it cozy in there. read more

Nice small bar with friendly staff and patrons. It has a small TV you can watch but you probably shouldn't come here on game day.

Bar tender was extremely rude. I would never come back. Wouldn't recommend ever coming here at all. Go to one of the other hundreds of bars and save yourself from uncalled for attitude. read more

Jackie's is a great place to grab a drink with your friends. It used to be my neighborhood bar when I lived around the corner and I could be found in there any night of the week. I have met a ton of great people at this bar and have developed many great friendships. The bartenders are fantastic! Some of the best I have met in Chicago (and I am an ex-bartender myself). Friendly, intelligent, witty, and attentive. The jukebox has a good mix of Country, Pop, Alternative, and disco/show tunes. There's a video poker/slot machine in the back and an electronic dart board. Greg is a mean Cribbage player too and will deal a game if asked. Please keep this in mind when going to Jackie's (esp. on Thursday nights): THIS IS A DART BAR! This bar participates in the WCAA dart league on Thursday nights so the board will most likely be taken by the League from 7pm until the wee hours of the morning. If you want to throw darts come on another night or expect to wait until 10pm or so before you get a turn. Always someone there willing to throw a game so don't be shy! The crowd is pleasantly mixed: gay, straight, single, married, young, middle-aged, locals, and strangers. Not the typical flaming gays or the obnoxious drunk breeders; no guys hovering over single women showering them with whatever knucklehead pickup lines they learned that week. Just good, genuine people from the neighborhood or, like me, formerly from the 'hood coming back to enjoy a brewski with the crew. Tell Greg "The Cowboy" sent you. read more

Simple dive bar but what else do you need? Jacqueline's is down the street from Joe's, another great dive bar in Lakeview. Excellent bloody Mary's and small enough to actually have a conversation with your group or your bartender. They decorate for all the holidays so you'll get a different experience each time you go! read more

I feel so lucky that Jacqueline's is my neighborhood bar. The owner is one of the sweetest people I've ever met and always runs inside when she sees my dog and I coming down to get him a treat. The regulars are also great and even though I only stop in once every other month, they always strike up a conversation. read more

Way too many people do know my name at Jackie's and it's always a good time. Juke box is great. Ted, Rog and Greg are truly fantastic bartenders, and the birthday shot is the best in Chicago. Best bar in boystown. All kinds welcomed. read more

Love this place! Jason, the bartender, is the best. I'm not really a bar person but I became a regular here because I love the atmosphere. It's great talking to Jason & lots of people bring their dogs in. Super chill. read more

Great spot to stop in while walking the dog. My little guy loves to snack on a treat while I sip an ice cold beer. Really a cool spot! Dog friendly as well. read more

Great bartender(Lee), great neighborhood clientele , great music all in a great little corner tap. Went in during a Cubs game( thank god I'm a Sox fan) and had the best time. Thanks to Lee I knew all the regulars in about 10 mins. And it was a free for all after that. Can't wait to go again. Thanks Lee, you're the best. read more

The other reviews & reviewers have truly overrated this establishment. If you can get past the glassware (which is far from clean), improper & unsanitary food serving methods, self-righteousness of the regulars and narcissistic bartenders this may be the place for you. Bottom line = there are far better "dive" bars in this neighborhood, do yourself a favor and keep walking. read more

The location is excellent, right on the corner of Broadway and Roscoe. The bar has a cozy feeling, not too big, not to small. The prices are reasonable and the bartender is personable. The only ding was the personalities of some of the customers. Especially a bleach haired, female that was playing darts. Her personality left a lot to be desired. Being a female myself, I recognize the behavior. She created a very negative atmosphere throughout the bar with her verbal bullying. Maybe she is one of those mean drunks, but in the meantime (no pun intended), she is running away customers. The business would do well, keeping her and people like her, away. read more

Fantastic bartenders. The kind that will learn your name and your drink, and have one ready when you start getting low. Very chill scene, just neighborhood folks that know each other and don't seem to get too rowdy. Got to take my picture with a patron's pet parrot! He even let me put him on my shoulder! Not that this is particularly useful information, but thats the kind of place this is - friendly...comfortable...always an interesting time. read more

Love this spot...stumbled upon it down the street from our hotel. Seems to be a super legit local watering hole. It was dog night, so we were immediately greeted by several pups Some great live jazz followed. Great bartenders too!!! We will return! read more

I liked this bar when I went there. It was tiny, but nice. The best part was the heater in the women's restroom (I went in winter.) The one thing I didn't like was since it was so small the U-haul boxes made the place even smaller. read more

If you want a chill dive bar in boystown, minus the boys, then this is the place to be! It's just lovely! And the bartenders RAWK!

After you go against my advice and go to the Closet and are kicked out for not being an employee or a friend of the employees, I suggest hitting this charming little dive. They actually do it right here by not using the Closets business model and instead are very nice and FRIENDLY. read more

Not sure why anyone would give this bar a negative review. I am extremely uncomfortable walking into a strange bar alone, but seriously, within 5 minutes of being in here I felt like I had been a 5 year veteran. I will DEFINITELY be coming back here on a regular basis! read more

when i lived in this neighborhood, this was my favorite hangout. greg and jason are awesome bartenders, and make perfect drinks!! a great place to hang out with all sorts of people- you'll never find a more diverse crowd, which i love. always some friendly to talk to in there! and being a dog lover, i i love that they allow them in there! moved to the burbs and don't get there as often as i'd like anymore but i miss it! read more

Nice little bar located near...or in Boys Town. I used to frequent this establishment back in the day. My friend Greg is the bartender...one of the best in the city! I worked there for about a month, and he showed me the ropes on how to serve drinks and get the ladies drunk, haha. Jackie is really nice, and the regulars are all very cool...except for one a-hole, Bruce. Just an angry old fock with a sh*tty disposition. Besides him, kudos to Jacqueline's! read more

This is a great friendly bar with a community vibe- lots of fun for all.

While walking down Broadway on a lazy Sunday afternoon, I spotted the Pride flag in Jacqueline's window and decided we should stop in for a drink. As soon as we stepped in it started a downpour, so it must have been fate. The day we were there they had a Meatloaf contest to benefit an AIDS charity. Lots of regulars there and they were very nice to the visitors. Jacqueline was sitting next to us and it was great to chat with her- very gracious. Super-friendly bartender whipped up his custom bloody mary (not from a mix!) and it was delicious. We will seek it out next time! read more

I popped in here two Sundays ago. It was late and rainy....I walked in and the bar was completely empty! I was hoping for a hot half naked burnette....but what are you going to do? a few min later another guy popped into to the bar..He seemed to be a regular...I practiced my dart game as I slugged my Heinkeen. I did ask the bartender...For hearing so much about this place where is the lively crowd? He said they were tired from a busy week. C.S.I. Special Victims unit played on the tv as the bartender and the regular discussed various issues. The bartender was nice and he was quick with the drinks...but there was no lively crowd or hot half naked burnet...what a let down..I'll be back! read more

This is one of those bars to go to if you just need a place to relax and grab a quick drink with friends. I have been here a couple of times with friends. We came here when the bars were too crowded on Halstead. The drinks are good, the bartenders are friendly, and located in a great location. There is really nothing exciting about this place, but it is a good place to unwind and have a cocktail or two. read more

This has been our go-to bar for several years now and we still love it. Greg, Roger, and Jason are all awesome. This place never disappoints and is always a great time. Definitely worth at least one visit. read more

It was pretty quiet for a Saturday night, but the drinks were reasonable and the bartender was friendly. Nothing to be that impressed about, but I have a feeling I might stop back in from time to time. read more

I have lived in the neighborhood for four years and will be moving soon. Jackie's is one of the spots I will miss most. A great Chicago corner bar with super friendly bartenders and regulars. read more

Cubs won World Series. A great moment. I live 3 minutes walking distance to Jacqueline's. I enter to have a beer or two after Cubs won. It is 1.am. People are having a good time and a rememberable moment. 108 years worth of remembrance. After the second beer, the security guy tells me to finish up. I ask nicely: "What time does the bar close?" He says " It does not matter" I say " It does, because there are 10 people drinking at the bar, and you do not insist to them that they finish up their drinks." He tells me to leave, that very moment although I had not finished up. I leave without any ado. He locks the door behind me. I tell him that he is not fair. He says " I do not give a shit." I stand outside the bar, and after a couple of minutes, I knock the door saying that I will cancel my bill. The bartender makes a few signs meaning he does not give a shit either. I call my credit card company, explain the situation and I and cancel my bill. I am a Criminology minor. I know to distinguish fair from unfair. If you go to this bar, just make sure that you use your credit card and be reimbursed in case you are mistreated. Nothing wrong with the bar. The owner should simply know how his employees run his bar in his absence. read more

It's very fun & funky. Seven starz after bartender Gregg made my second round. And darts near the restroom door. read more

See all

i loooove this bar! its the perfect little dive in lakeview! me and my boyfriend love to play darts and just chill out and jacquelines is the perfect bar for that! We also think that Greg is a faaabbbulous bartneder! so if you want a chill evening to throw a couple darts or watch the game you wont be disappointed! read more

I had the pleasure of Jacqueline's a few times on my last trip to Chicago, thanks to one of my friends who frequents this amazing establishment on the regs. Being from out of town, I had some reservations walking up to this bar that oozed 'neighborhood bar' that Thursday night, I know that some of my regular haunts can be a bit hard on new people. All of my fears were smashed as soon as the door opened. The bartender, Jason, greeted us with a welcoming grim and sassy wit that immediately let me know I was in the right place. Drinks and conversation flowed, everyone was welcoming and inviting, and the music was great. It was a place that you feel comfortable and welcome in, regardless of it being your first time, or your 50th. We also visited for New Year, it was after midnight, and people were in great spirits. We were able to find room to join the celebration, welcomed with open arms, and encouraged to enjoy some of the amazing food that Jason had made for the bar. Jacqueline, who is as beautiful as she is personable, was in the bar welcoming all, being a most gracious hostess (dressed to the nines of course). Prices are great, selection is wonderful, and music selection is brilliant. Anytime I can crush Chumbawamba under the boot heel of Metallica and the masses are pleased, well then, that is an amazing time to be had. I can't wait to go back! read more